Showing posts with label transfeminine. Show all posts
Showing posts with label transfeminine. Show all posts

Monday, September 1, 2025

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

Sunday, August 31, 2025

Long Labor Day Weekend

 

Image from Anna Storsul
on UnSplash

Labor Day weekend is upon us in the United States which gives us an opportunity to take an extra day off and think about what got us here and how close we are coming to losing it.

Even though I have never been in a union myself, I am an amateur historian and know what unions did to transform this country. All you need to do is some basic research on how bad working conditions were in the steel industry as well as coal mining and elsewhere to see what unions brought about. So, on Labor Day, I salute them.

Elsewhere, the weekend this year features some beautiful weather with sunny blue skies and very low humidity for a change around here in the Ohio River Valley (Cincinnati.) Of course, the early fall like conditions won’t last forever and soon we will be back into summer’s last call. In a couple of weeks, my wife Liz and I will be headed for the East Coast, Boston, Maine and more so I am hoping for the reasonably good weather to hang around until then.

By now, you may be asking what does any of this have to do with being transgender? The answer is it has everything to do with being myself as a transfeminine person. Since this marks our fifth bus tour over the years of hanging out with other cisgender women waiting for my chance to use the bathroom, I still have lingering paranoia with using women’s rooms which goes back to my earliest days of cross dressing in public. Even though I have not had any problems in the past with anyone else, I still have the idea it only takes one bigot on the bus to ruin my trip. At least, this time we are traveling through more liberal blue states, so I won’t have that to worry about. As I said, my lingering fear is subsiding, so I can concentrate on having a good time and seeing the sights of New England. The last trip we were on a woman asked if Liz and I were sisters, so you cannot get more validation than that.

Closer to home before we leave, tonight we are going to dinner at our favorite restaurant with her son. It is another venue I have rarely ever been misgendered in and have never had any serious problems. It always feels good to just exist and enjoy myself since I worked so long and hard to get here as a transgender woman. The more I can fly under the gender radar in today’s world, the better I feel.

Before we go, I will have to shave closely, apply moisturizer, powder and lipstick before I change out of my The Ohio State sweatshirt and into a frilly feminine top and brush out my hair. All of which are still fun for me to do. Not just something I have to do to present better in the world.

Finishing out the day, it will be time to head home and watch the end of summer Cincinnati fireworks display. The display is always huge and attracts nearly a million people on both sides of the Ohio River. Back in the day, when I was younger and another person, I used to come down every year for the Booms. But age and mobility have caught up to me, taken their toll, and we just watch them on television now. Then let the out-of-control neighborhood idiots set their fireworks off and scare the animals and any near veterans with combat PTSD. Out of the two cats Liz and I have; one hates any sort of loud noise.

As with many other holidays, Labor Day presents yet another milestone in my transgender life. I can remember quite vividly when I used alcohol on holidays to dull the pain of not having the chance to spend them as my feminine self. I was fortunate to have escaped my closet and the control alcohol had on me before it was too late. It turned out it was all in front of me all along if and when I had the courage to reach out and seize my opportunity to transition and just be me.

I guess you could say, I needed to labor to do it, but it was worth the effort. When we toast ourselves tonight with our Margaritas, I will propose a toast to all the work we three have put into to where we are today. And, to all of you, no matter where you are today, have a chance to pause and celebrate the gender journey you are on, or have yet to do. Buckle up! It is one hell of a ride. 

Saturday, August 30, 2025

Out od Sight...Out of Mind?

 

My wife Liz on left and daughter on right.

Most if not all transgender women and trans men go through phases in their life when they think gender issues are out of sight and out of mind. It is not entirely different than the moves some state legislatures (Ohio) are going through to try to erase us in the public’s eye.

If you read my posts at all, you know how I feel about that. Trans people have always been around and always will be. Attempts to erase us will be futile. On a lesser but just as important level, we try to erase ourselves by purging our lives too. I know the guilt of being a cross dresser or transgender woman became too much for me to handle and I threw out most of my treasured feminine wardrobe and makeup. Out of sight, out of mind I thought.

In the long term and the short term, none of my purges worked because I refused to accept my true self. I had my life all backwards and I was not a man who cross dressed as a woman, but a woman who cross dressed as a man. Until I figured it out, I kept trying to hide the obvious. Of course, it did not help as I started with two gender strikes against me. I went through birth as a male and then had to go through male puberty and suffer from what I called testosterone poisoning. My body kept the bullies away and allowed me to play sports but caused me torment when I was in front of the mirror trying to be a pretty girl.

As life went on, I thought for the most part I had learned to live with my gender dysphoria the best I could. To this day, though, I wished I could be a “normal” male. How much better could my life be if I could socialize with the other males around me without feeling as if I was an outsider. I grew tired of being an actor inside my own skin. The only thing I could do was mentally try to get rid of my feminine self. Taking me full circle back to why I was keeping all those clothes, wigs and makeup anyway. It took me by throwing them away to understand exactly what the problem was. It was not a problem unless I it made one, which I was by purging again.

Deep down I knew I was wrong and very shortly I would be re-stocking my fashion and make up to try my best to present feminine again to myself and the world. However, I was very stubborn and my male self-hung on way too long refusing to give up on his hard-earned male privileges. Life could have been much easier by staying where I was in the gender world, but it was just wrong, and I couldn’t. The more I lived as a transgender woman, the more natural I felt, and I never wanted to go back into the male world I had made the best out of.

Increasingly, the male purge was looking to be the one I was going to attempt to make. I was sick of living a gender lie, and I wanted to reverse my idea of living. I wanted to feel “normal” again but this time around a group of cisgender women. Flipping the gender script on my life was the most difficult thing I had ever attempted to do, but somehow, I made it through the female gatekeepers and did it.

In my new transfeminine life, I was rarely out of sight and out of mind. I had a lot of help to do it who I will never forget. I had spent my whole life chasing a dream and had finally achieved it. As I symbolically and literally gave my male clothes to charity, I stopped to remember the entirety of what I was doing. I was giving up the male side who had dominated me for so long. To be sure, he had served me well, but it was time to go, and this final purge was a triumphant one for my transgender woman who had waited so long to live. After all, she had her life taken away several times when she was purged nearly out of existence.

She survived and so did I and everything in her power to make things better. When I worried how I would be perceived in a new world. She had my back when it mattered, and it did. Even in the days when she had to give me quite a bit of tough love. She had to watch me grow through my ill-advised teen cross-dressing years into a presentation I could be proud of or at least satisfied with.

Out of sight, out of mind never worked for me.

 

 


Thursday, August 28, 2025

Gender Immigration

 

L'eggs said it best.


With all the negative publicity being brought to the new immigrants to this country by the orange felon/pedo in Washington, I thought it might be time to connect the dots to my own immigration. A gender one.

My immigration plans began as a vacation. I was tired of the male world I was competing in and taking a break as a cross-dressed girl in makeup was a great way to escape my life. Little did I know, from these humble beginnings, I was starting a lifelong journey which in many ways, I am still on over a half a century later. Had I known, I would have ever attempted to undertake such a radical immigration.

Early on, I was just looking to grab the so-called low hanging fruit of cross dressing. I enjoyed the feel of the clothes, all the way to the thrill of hose on my freshly shaven legs. Then, I slowly began to realize so much else was happening. Increasingly I wanted to be more and more like a girl and started to wonder about pushing my male self out. It was difficult because I came from a highly male dominated family. As I pushed forward, my immigration into the feminine side of life became more intense. I tried my best to acquire new more fashionable clothes and even bought my own makeup and panty hose. Do you remember the “L'eggs” panty hose which came in plastic egg shaped containers which it seemed you could buy everywhere, and is still made today. I learned the hard way; how easy it was to destroy a pair when I unfortunately ran one of the legs. Ruining my outfit.

Progression was slowed by a late-teen collision with serving time in the military due to the Vietnam war. Obviously, I could not bring any of my “stash” of women’s clothes or makeup with me, so I was stuck. No more gender immigration for at least three years of my young life. There were several major positive things which happened for me while I was stuck being a man in the Army. A prime example was all the traveling I was able to do around the world in places such as Thailand and Europe (Germany). The whole process enabled me to keep my mind off my gender issues and set me up with the idea I could outrun my problems. Which, of course, turned out to be impossible. Which should be the topic for another blog post.

After the Army, my life changed again as I entered the world of parenthood. Being a parent of a daughter was an unexpected but pleasant surprise, and my gender immigration was put on hold briefly again. I say briefly, because I discovered my transgender issues ran deeper than I had thought. My presentation as a novice transfeminine person was coming along. My first wife did not care, and I was able to explore my potential future as a gender immigrant at events such as Halloween parties. Each party to me represented a chance to see how I was being accepted as a woman in society.

After a few years, I ended up divorcing my first wife and marrying my second. She also knew about and accepted my cross dressing from the beginning of our relationship but never accepted me being transgender as I immigrated towards being a woman. My male side was like being the Titanic, slowly sinking and then picking up speed with her fighting me all the way. It turned out, the issues I was facing were like the tip of the iceberg. With most of it being hidden from everyone. Including me. She tragically passed away before the final resolution in our relationship was ever decided.

When she moved on to the other side of existence, it was left up to me to decide the future of my immigration. I had certainly paid my dues by taking on all the menial and not so menial work of being a woman. I was on gender affirming hormones and was living as much as I was able as a transgender woman, so I was close to filling out my immigration papers and was ready to go into a world I had only dreamed of. My presentation had improved to the point where I was not the most attractive woman in the room, but I could handle myself to the point where most of the world just did not notice me. So, my immigration was more successful than I ever thought possible.

Perhaps the best part of immigrating was learning to accept and love myself for who I really was. Which meant all the hassles I had over the years as I tested out the world, made my immigration worth it.

 

 

Tuesday, August 26, 2025

More than Theatrics

 

Christine Jorgensen circa 
early 1950's. 

Deep down I knew being feminine for me was much more than a theatrical exercise dressed in front of the mirror as a girl. I wanted to do more than just look like a girl; I wanted to live like one. I wanted to be the one with the pretty clothes that all the boys admired.

It turned out I was ahead of myself as far as my gender dysphoria was concerned. Gender dysphoria, as well as the term transgender had not yet caught up with the public at large. It was still transvestite, transsexual or Christine Jorgensen or nothing for me as far as having any idea anyone else in the world was like me at all. Perhaps you may not know it, but Jorgensen was supposedly the first widely known transsexual to come out with the very public news of her gender realignment surgery in the early 1950’s.  No theatrics involved, just a lot of publicity, I guess.

I thought of Jorgensen and the gender loneliness I felt the other day when I got to watch “Some Like it Hot” on our local PBS station. I was approximately ten years old when the film was released in 1959 and I remember being mesmerized by the idea men could be women at all. Even still, I don’t think, or remember, if I connected the dots yet to how I was feeling about myself. I was still very much stuck in the everyday struggles of being a boy.

When the internet became popular, I began to discover a whole, wide wonderful world of gender possibilities. Including a term which I had never heard of before, transgender. As I understood the term, it took away all the possible theatrics of just looking like a girl and brought up the possibility of living as one. At that point, I began to wonder if I was a cross dresser at all, and not more. The only thing I thought I knew was I was still in some sort of middle ground as my gender dysphoria went. I felt much more that I was so much more than the average cross-dresser, but not quite there yet as far as I wanted all the surgeries Jorgensen and others were going through.

To maintain any sense of mental stability at all, I began to explore the world the best I could to see if I fit in with this new transgender term I was reading about. My best and exciting evenings came about when I was able to be invited to and attend small diverse parties at a transsexual’s house in nearby Columbus, Ohio. It was there I learned about the dangers of being trapped by a much bigger and powerful man, all the way to being picked up by a lesbian I had never met before. Most importantly though, I was there to observe and learn anything I could from the hostess, a transsexual retired fireperson from Columbus who was headed to surgery. Michelle was beautiful and I was dazzled. I discovered there were no theatrics from her, she was as real as could be and I wondered if I could ever achieve what she had.

The main thing I did learn was, my deep feelings about living as a transfeminine person may not go the same way as Michelle’s did, but it was possible for me to live my own successful life as a woman if I tried hard enough. That is when I learned to put my cross-dressing theatrics away which had served me well and I entered another phase of my life. Michelle was beautiful and exotic in her own way, but I could do it too, just in my own way.

I would be kidding myself and all of you if I said finding my new self was ever easy. I needed to make all the difficult decisions about risking everything in my life which was important to me. Such as a loyal, long-term spouse, family, friends and good employment. The same things we all go through as we struggle to transition as a transgender woman. When I finally decided I needed to go the distance and give all my male clothes to charity, the weight was off from my shoulders to not live a theatrical existence as a man anymore. I spent over fifty years fighting a gender battle I could not win as the cards were stacked against me.

I was able to put all the gender questions I suffered through in my past and build a new transfeminine life the best I could. I just had to quit the theatrics to do it.

 

 

 

 

 

Monday, August 25, 2025

Come Out Swinging

 

Image from Chase Li
on UnSplash.

Often, I write about running home to dress in my skirts and put makeup on to hide the failures I was feeling as a male.

My plan worked well until I discovered I was advancing so far and so quickly as a novice cross dresser or young transgender girl, I was unknowingly destroying my hiding place. Someone turned the light on in my closet and suddenly I had nowhere to go. I needed to come up with a plan to come out swinging or I was doomed. In addition, I still had to be very careful not to be caught and end up in a psychiatrist’s office declaring me mentally ill. Then I would really have nowhere to hide.

The better I became at the art of makeup and dressing myself, the more I needed to consider what I was doing and wondering if I should come out swinging at all. The problem continued to be, I was building more male privileges in the life I was living. My life was like shadow boxing myself as I sought out answers. Like most of you, I was risking a lot as I came closer to pushing all my life’s chips to the center of table and betting it all on the fact I was a transgender woman all along.

Then I went into my highly recommended experimentation years of my life. In order to have any sort of an idea if I wanted to live as a transgender woman, I needed to walk a mile in my new high heeled shoes. Those were the scary yet exciting nights when I escaped the gay venues I was going to and began to attempt to establish myself as a regular in lesbian and other straight venues I was used to going to as a man. When I did, I discovered I needed to make another transition from serious cross dresser to transgender woman exploring the world. To my amazement I was successful when I went to venues such as TGI Fridays and socialized with other professional women. Maybe I did not have to swing so hard after all to escape the dark confines of my gender closet.

To be sure, I still had setbacks when I came out into such a different world, but I had enough gender euphoria to realize I could live out my dream if I worked hard enough at it. At first, I suffered from the “what I thought a feminine life would be” syndrome. I was trying to put all those years of closely watching how women lived into actual practice without paying my dues in the world. While I resented the fact, no one would let me see behind the cisgender woman gender curtain, I was becoming a victim which did me no good in the short or long term. So what if I did not understand what I was doing wrong, I just had to figure it out and do better.

One of my major problems was solved when I finally came to the conclusion I was never going to be accepted as a cisgender woman, but I could find my own version of womanhood on my own path. That is when I started to wear only one wig, settled on one name and began to build a new serious life as a transfeminine person in the world. As I settled into a new life, I found that many people (especially women) appreciated my honesty in a world of fake people. I was surprised at all the female attention I received and was relieved I did not have to attempt to change my sexuality.

The more I changed, it seemed the more I stayed the same as my long hidden feminine soul took control finally. I was dealing with life on a one-to-one basis for a change without having to swing away all the time just to survive. As HRT hormones entered my life, it was just another example to me of what took me so long. My body took to the gender affirming hormones flawlessly and I was off to yet another transfeminine adventure. My age and hormonal status led me down a new road of dealing with confrontations, no more could I try to macho my way through trouble, I needed to take the feminine path and try not to get into a situation I could not get out of before it happened. Or no more swinging away for me. I needed to use my brain for a change.

As I have pointed out in previous posts, I was never a good athlete and could never hit a curveball when I tried to play baseball. I finally took it all to heart and quit trying to hit a curveball altogether and settled into watching the boys play baseball (and girls too) when I did not have to play. I was tired of banging my head against a hard gender wall and ended up where I always should have been as a transgender woman. I just wish I had not been so stubborn when I was doing it and had shed my male self-long before I did.

 

Friday, August 22, 2025

In Over my Head

Image from Alexander Mass
on UnSplash
In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  


Thursday, August 21, 2025

The Blues

 


I have not been ashamed over the years to document my struggles with depression, which was finally diagnosed as being Bi-Polar by a gender therapist I was going to years ago. Fortunately, the therapist was the first of several who did not try to connect the dots between my mental health issues and my depression. Saying one caused the other.

What was happening was, when I got the blues, I was down for days, not wanting to even get out of bed. Having said that, I was able to break the depression on occasion by cross dressing and going out into the world as a novice transgender woman. Breaking the hold of the blues was often very brief when I needed to return to the very mundane male world I was stuck in.

In addition, I was doing very little to help myself. I drank heavily, not considering how much of a depressant alcohol was and my favorite music to listen to was the blues. Regardless of my gender issues. As you can tell, outside of the Bi-Polar medications I was taking, I was doing very little to help myself. With or without the help I received, I managed to make it and eventually thrive rather than just survive. Regardless of my second wife calling me the “pretty, pretty princess”, I still took a lot of pride in my feminine presentation. The better I looked, the fewer blues I needed to conquer in my life because for once, I was doing something positive for myself.

When I needed the Veteran’s Administration’s health care in the worst way, they really came through for me. I was going through hard times when my restaurant closed financially and could not afford my medications when one of my employees suggested turning to the VA for help. It was about this time too when the VA approved gender affirming hormones for veterans so I could help myself on two fronts by making an appointment. It turned out that what I needed was an appointment with a therapist for both of my issues. My depression and my gender issues. By the pure luck of the draw, I was assigned to a therapist who had knowledge of my depression and my gender dysphoria. I was going into my first visit thinking I would have a difficult time explaining how my Bi-Polar depression had nothing to do with my gender outlook.

I never had to connect those imaginary dots with my new therapist. She had a good understanding of the needs of the LGBTQ community and what it meant to me. Once again, all the paranoia I had built up was wasted and my depression meds as well as my HRT meds were approved. It was the help I needed when I needed it at the lowest part of my life.

Regardless of all the good news I discovered, I still had to translate all of it into my real life which was changing dramatically. I was going out more and more testing out my interactions with the public. Building a new life was as difficult as I had imagined and the struggles I went through sent me back into the blues when I thought I would never make it as a transgender woman. To be completely feminized by no one else but me turned out to be a daunting task because I was starting from near to point zero. Very quickly, I quit being a victim and turned the tables on my male self who was fighting for survival, but not before I tried various self-destructive things such as trying to kill myself. The blues were literally trying to kill me.

In my limited understanding of both issues, I fought for my entire life, both depression and gender dysphoria could be caused by chemical imbalances in my brain. So, I had no real chance to battle them. I was born to a high-risk birth rate mother in the days when the medication DES was routinely prescribed. DES supposedly flooded the uterus with estrogen hormones which could have affected my future gender issues. Of course, now I will never know if my lifetime of struggle to fit in with males was doomed to begin with and now depression is widely believed to be caused by a chemical imbalance in my brain which I think I inherited it from my mom. One way or another, I feel fortunate to live in an era when medications are available to treat my depression.

In many ways too, the blues are an outlet I miss in my interactions with today’s world. As the mid term elections rapidly approach, I am preparing myself for the barrage of anti-transgender propaganda from the Republican party here in Ohio. Knowing what to expect won’t make it easier for me to survive. As always, I will just have to. With or without the blues because every little thing is going to be alright.

 

 

Wednesday, August 20, 2025

Confidence is your Main Accessory

 

Image from 
Jon Tyson on UnSplash.

Some assume I have reached the point of life I am at, through very few challenges.

The truth is that I faced many challenges along my very long gender journey to living fulltime as a transgender woman. I write about many of them often. As I look back, the one main challenge I faced was having the confidence to move forward to my strong dream. Perhaps the earliest confidence I needed was when I walked down our long driveway dressed as a girl to check the mail. Hoping someone would notice the girl in a miniskirt out of the house on a winter’s day without a coat. Then hoping no one would see me and somehow report me to my parents. Nothing ever happened, so I gained the confidence to keep doing it.

The problem was, there were only so many trips to the mailbox I could take to feel good about my cross-dressed feminine self. Here I was taking all that time and effort to feminize myself and having no outlet except the mirror. I was frustrated in my little closet which I had no idea of how to escape from. I was like a caged animal, I knew I wanted out of the cage, I just didn’t know where to go when I escaped.

As the years passed by, I traded going to the mailbox with a yearly trip to a Halloween party. Even though it took me years to get it right, I finally figured out how to figure out a “costume” which helped me to build my confidence that I could present well enough to get by in the world as a woman. My goal always became to be mistaken for a woman in a costume, not as a man dressed as a woman and I achieved it. From there, my problem became Halloween only happened once a year, and what would I do the rest of the year about my growing gender dysphoria. My final decision was a simple one, if I had the ability to do it. I would have to manufacture my own reasons to sample the world as a novice transgender woman and see if I had the same positive feedback I received on Halloween. I discovered most of the world did not care about how I was dressed, and I gained the confidence to do more.

I made it to the point where I began my “bucket list” of things to do as a transfeminine person. Or could I do other things that women do in their everyday lives and succeed. Every time I did something such as taking myself out to lunch, or negotiating a bookstore and buying a coffee, I checked them off my bucket list and proceeded to move on to more difficult interactions with the public.

Of course, not everything I did was a success. I was told to leave a venue I thought I was a regular in one night when three drunk guys thought it would be fun to play “Dude Looks Like a Lady” on the jukebox over and over again. Initially it hurt me, until I got my confidence back and found another venue right up the street. My success was complete when the crew of the place I was asked to leave found me one night. They told me the manager who told me to leave was fired for drug abuse and they wanted me back. Retribution was mine as well as a real boost to my confidence. It felt good to be wanted as their token transgender woman.

Even so, to this day, I wonder why my confidence is so fragile. In September, my wife Liz and I are taking another bus tour. It’s our fourth one, and this time we are traveling from Ohio to Boston and then up into New England by train. Even though, I have never had any real problems with anyone else on the trip before, in the back of my head I still worry about some right-wing woman questioning my gender and ruining my trip. I am sure I am just paranoid and should be worried about catching Covid again and ending up in another hospital. Which is how our last vacation ended up. Hopefully I can get an updated vaccine just before we go. Which will build that part of my confidence.

The only way I know to build your confidence is to keep being yourself and improving your presentation as a transgender woman or cross dresser if you prefer. Perhaps it will always be fragile like mine is and it is something we always will have to deal with. One thing is for sure; you cannot build it by hiding yourself away. Expect some setbacks and keep moving forward as you are building a new future. It is a huge step forward. Having nice fashion and applying beautiful makeup is wonderful but it all means nothing if you do not have the confidence to pull the picture together. Humans are like sharks and they will know something is wrong if you let them.

 

 

Tuesday, August 19, 2025

In Over my Head

 

Image from Wilhelm Gunkle
on UnSplash.

As I thumbed through my new feminine workbook, I sadly discovered there were no chapters on what to do if I got in over my head. In my well-built male world, I had been able to figure out strategies on what to do in times of duress. I could choose to stand and fight, try to bluster my way through, or just run from the problem.  None of which was available to me anymore on the gender path I was on.

Even though I was blessed with a healthy male body which was slightly bigger than the norm, I had hated the changes testosterone made to it when I had no choice but to go through male puberty. Very quickly, I grew past the sizes of my mom’s clothes I was trying on and had to find other ways to build my wardrobe on the very limited budget I was on. My newspaper route money, along with the small allowance I got for helping around the house, just didn’t go far. Still, I was able to sneak out of our rural home under the pretense of visiting my grandma who lived downtown and do some shopping for makeup and hosiery. I just remember how incredibly overwhelming the makeup selection was and how much I was over my head with my selections.

After I was able to smuggle my purchases past grandma and my family, then I needed to work earnestly on how to apply the makeup I bought and not look like a clown. After looking in the family mirror and feeling like a clown in drag, I knew I was in over my head and just had to find a way out, or in as it turned out. I wanted out of the male world and into a feminine world. The mirror was wearing off, and I needed to improve my presentation, or I was doomed to forever occupy a male spot in the world where I knew I was not in over my head. The white male privileges I was building up were just too easy to not take advantage of. Ironically, all the good I was accomplishing in the world with my family, friends and job was frustrating me because, deep down, I did not want it.

What was happening was my frail mental health was being destroyed by all the gender ripping and tearing I was going through. One day I was a successful man and the next I was working to present my self as a woman was very destructive to my everyday existence because the whole process took me back to my gender fluid days when I was a kid. Back in those days, no one knew about the gender fluid term, or used it which put me in over my head before I even really started in life. Remember, I grew up in the pre-internet dark ages when anyone who cross dressed was considered mentally ill. At least I knew, even though I might be alone as a transvestite (another term from the dark ages), I was not mentally ill.

I barely survived the dark ages when I did learn there were actually individuals like me who wanted to dress as women. I would be remiss if I did not mention Virginia Prince and her Transvestia publication at this point. It was my lifeline to the cross-dressing world and opened my closet for the first time. When the light came flooding in, at first, I was blinded, and it was difficult to find my bearings. My first transvestite-crossdresser mixers I went to left me more confused than ever before. I knew I was in over my head when I saw and occasionally chatter with a few of the ultra-feminine women who I could see no masculine traits at all and on the other hand, I knew I was innately more feminine than many of the cross dressers I met. So, I left with more questions than answers.

I was caught in the same place for years as I explored the world looking for myself. Surely, along the way, I found myself in over my head as I transitioned but I kept going anyhow. Too stubborn to quit and waste the new feminine privileges I was working so hard to gain. To use another example, I threw myself into the deep end of the gender pond before I had learned how to swim. I gave myself no choice but to make it. Fortunately, all the mirror time working on my presentation as I wanted to be like the beautiful cross dressers I saw in Transvestia came back to help me. If I could present myself to blend in with the world, it gave me one step up to make it as a transfeminine person.

I certainly was in over my head enough to earn my right to play in the girl’s sandbox, and fill out my gender workbook.

 

Monday, August 18, 2025

Transgender-When Life Throws you a Curve.

 

Image from Chu CHU on UnSplash.

It’s baseball season as we head down to the “dogdays of summer” around here in Cincinnati. As I have mentioned many times, the gender gods allowed me to take my passion for sports with me when I transitioned from male to female. This year, I have been completely emotionally immersed in the Cincinnati Reds professional baseball team. So much so, sometimes I feel guilty about my involvement.

Overall, though, life threw me a real curveball when it came to sports. For several reasons, athletics helped me to keep the bullies away, since I was doing “boy” things. As I played, I found I could not hit well at all, primarily a curveball and resorted to running home to my dresses and makeup to feel better about my failures. And I did, which solidified my deepening idea I should have been a girl all along. Dressing in my pretty feminine clothes certainly felt better than crying in the shower after I committed a key error or struck out to end the game.

As time went on, I faced the reality of non-athletes everywhere, life had thrown me a curve ball I just couldn’t hit. Somehow, I just needed to adjust and become the fan I am today and quit being a victim. I think perhaps it was my Army duty which took any idea of self-pity away from me. So what if my draft number was twenty-three, I would just have to enlist for three years to make the best of it. Plus, the entire routine of basic infantry training took any idea of being a victim away from me. At least I was not one of the guys crying on the night bus to Ft. Knox in the middle of a Kentucky winter. Somehow, I would have to make the best of a situation I did not want to be in.

It turned out, that idea carried right over into my gender dysphoria. The older and more experienced I became as a transgender woman, ended up clashing with my increasingly successful male life. Life had thrown me a gender curveball, and it was not fair but the problem was mine to deal with.

Initially, I kept striking out on my path to transgender womanhood. I was woefully unprepared for the world I so desperately wanted to enter. The path was quite dark with many bumps and curves, so I needed to be careful with the high heeled steps I was taking. Perhaps the most important problem I faced was when I was completely outed as a man in a dress was quickly going home and attempting to figure out what I was doing wrong. Was it my fashion, or my makeup, or what?

This time I refused to be fooled by a gender curveball and hung in there until my life began to change for the better. Slowly, I was being accepted as my true transfeminine self in the public’s eye. I was not hitting any home runs yet, but I was making contact with the public and was successful.

Incredibly to me, the more contact I was making, the more I needed to make. In particular, women were curious what I was doing in their world and drew me into conversations which were uneasy for me in the beginning. Life was throwing me curveball after curveball, and I became halfway decent at making contact with the strangers I met. I think too that after the public met me, more than a few of them reacted to the fact that I was a person who was living with their truth. Then I needed to catch up and respect myself for living my truth. Which was difficult for me to do for years.

Ironically, at that point, I went to work for a company which would not accept any of their successful managers being victims. I carried their training over into my real life and was better prepared for any and all setbacks I encountered. I began to see my supposed setback in life just could be a positive if I made it one. Not so much different than when I went to Army basic training wondering how I was going to make it without my cross-dressing crutches.

After immersing myself in the world of cisgender women, I came out as a better person. Certainly, well rounded in how the two main binary genders interact with each other. I could not ever make it as any sort of an athlete, but it turned out I could as a transgender woman. A journey I came to respect many times along the way.

 

Saturday, August 16, 2025

The Only Constant is Change

 

Image from Brad Starkey
on UnSplash

In life it seems, the only constant is change. Especially for transgender women and transgender men. As with most of you, my life of change started quite early when I started exploring my mom’s foundation drawer. To make matters worse, I then started raiding her makeup collection.

As I viewed myself in the hallway full length mirror, little did I know what a long trip I would embark on to battle my gender dysphoria. My male self was strong and put up quite the battle when all along my feminine self was plotting how she could win the war. All he could do was resort to typical male actions and reactions such as internalization of the gender problems all the way to completely running from them.

Change became reality when I started running from my problems by changing jobs and moving my family several times. My first move took my wife and I from our native southwestern Ohio home to the radically different environment of the New York City metro area. I was naïve and thought moving to a more liberal area of the country would provide me the opportunity to pursue my growing serious cross dressing “hobby.” Nothing of the sort really happened except a couple of times. The first of which was when I made the journey out to Long Island to attend a cross dresser – transgender mixer. I was so successful that I was carded at the door to prove I actually was a man.

The other example was a Halloween party I was invited to by a fellow manager of the restaurant I managed. Somehow that night I managed to escape the criticism of my second wife who wasn’t going with me anyhow and dress the way I wanted to. I chose my favorite wig, short dress and heels and slipped out of the house. Away from the unapproving prying eyes of our landlord. The evening turned into my dream scenario when I found I was going with several other tall and sexually dressed women as I was. The ultimate camouflage was I fit right in. My successes fueled my ego and pushed along my changes. For the first time in my life, I began to believe I could achieve my ultimate dream of living as a transgender woman. If I was fooling the world on these evenings, why couldn’t I do it more.

In the short term, my male ego hurt my ability to change. Being briefly accepted as a woman only pushed me on for more change. Leading to huge fights between my main feminine gatekeeper (my second wife) and myself. In typical male fashion, he oversimplified the gender problems with the same old results. It was time to run again and move from NYC back to a different part of Ohio. This time, to a very rural area along the Ohio River. Surprisingly, change came easily to me in this rural area of Ohio. I was able to cross dress and do the grocery shopping as well as other trips.

Still, change haunted me and I felt the need to find a job in Columbus, Ohio where I had been successful in the past in the crossdresser-transgender community. I felt if I could go back there, I could again fit right back in.

This move or change ultimately led me back to my hometown which was close to Columbus. I had come full circle with my changes which led me to finally face my gender reality. I was and had always been a woman at heart and had made my own way down difficult paths to find her. Plus, I was so tired of running all the time, so I did not have to accept the only constant being change. The only constant was my whole life as a male was a lie, and I had to do something about it.

I ended up taking advantage of all that I learned the years I was a novice transgender woman and using the lessons to make my transition more flawless. For once, I was changing in place as I threw my mirror out the window. I started using the public as a mirror to see how well I was presenting as a transfeminine person and went on to live my life.

For me, the final straw which ended my ill-fated male life was when I changed my life for good and started HRT or gender affirming hormones. I could not believe all the changes I went through and how good they felt. I know all people go thru changes in their lives but not to the extent most transgender persons do. It is certainly a difficult journey and not recommended that you take the path I took.

Thursday, August 14, 2025

You Make a Terrible Woman

 

JJ Hart on left. New wife Liz on right.

As I was initially coming out of my intensely lonely and dark gender shell, I dealt with quite a bit of guilt. Especially when my wife called me a terrible woman. I initially thought she was referring to my looks, which she told me she wasn’t.

My second wife was also fond of telling me coming out was all about me which as I look back on it, she was right. My transition was all about me, and I was completely immersed in it. Every time she even made the slightest move to interact with me, I shunned her as I was scared, she was just going to be negative. To be successful, I needed to do it alone it seemed.

I am sure the progress my wife saw in my overall presentation made her feel insecure about the future of our marriage. No matter how guilty I felt about the journey I was taking without her, deep down I knew I had to stay on my path if I was ever going to have a chance to achieve my dream of living as a transgender woman. Which my wife was dead set against.

As I progressed on and on the guilt grew, I was having. Here I was jeopardizing a good marriage, family and job just to wear women’s clothes and makeup. My problem was, I was still refusing to accept the truth about myself. In other words, my desire to be a woman in any sense of the word ran much deeper than just looking like one. When my wife told me I made a terrible woman because I hadn’t paid my dues past looking like one, I knew somehow, I needed to set out to learn what she was talking about, regardless of the guilt involved. To survive, my transition had to be just about me, and I stubbornly pushed forward.

The problem was, the more guilt I felt, the worse my mental health became. I did not know who to listen to, the world at large or the person I was closest to. The world at large was slowly coming to accept me as a transfeminine person while my wife was as standoffish as always about my progress. What she did not know was I was making the strides needed to prove I was not a terrible woman and in reality, a fairly likeable one. Or at least I was trying to.

Time marched on, and my guilt increased to the point where I committed suicide or tried to. When I failed, the entire self-harming episode left me with further problems with my guilt and mental health, so I sought out therapy. Fortunately, I found a good therapist who understood depression and the transgender community, and my life began to improve again. My therapist told me it was alright to feel guilt about the gender transition process and sometimes you must leave loved ones behind so you can live. Beyond all of that, she taught me extreme gender dysphoria was difficult to deal with and before long, our in-person meetings at the Veteran’s Administration were between her and my authentic self. What a relief!

My guilt subsided as my joy increased in my life. Sure, I still had rough spots to contend with, but with my overall knowledge of the world and what to expect, I knew I had finally overcome my fear of actually “making” a terrible woman. In reality what happened was I had the chance to live my way through what my wife told me and in addition. I was not making anything. I already was a transgender woman and had always been. I was just guilty of trying to hide it and internalize it too long. Surely, it was all my fault, and I never had the chance to apologize to her because of her untimely death from a massive heart attack at the age of fifty. I wanted to show her I had paid my dues in the world, and, at the least, I hoped we could be friends. Actions speak louder than words and I know she would never back off from saying I made a terrible woman and in turn at least like the new me.

In life, we rarely have a chance to make a second impression, and it has been nearly an impossible one for me since most of the people I knew as a man (that mattered) had passed away. I needed to concentrate on the new acquaintances I met as a trans woman who never knew my old male self who in his own way had passed on also. Since I did not have a difficult time making and keeping friends in my new life, I must not have been a terrible woman after all.

Wednesday, August 13, 2025

Out in the Testosterone World

Hair by JJ Hart, Beret hand beaded
by "Liz T Designs

Just a short post today as I just returned from braving a testosterone heavy environment. More precisely, it was time to get the oil changed in our car, which was slightly overdue. By the time I was done, I wished I had a dime for every tattoo I saw on the completely male staff.

For some reason, any trip to a male dominated (such as auto workplace) has always caused my gender dysphoria to flare up. Even after all these years that I have been out as a transgender woman, I still feel the same trepidation. Which makes me feel even more frustrated with myself.

This morning, as I pulled the car into the next available bay to be serviced, I cannot be sure, but I think the manager called me the dreaded “Sir”. But, as the work progressed, he became increasingly nice to me. I never know if it is the result of age privilege but at least he never called me “Sir” again. Very soon I was on my way to my next stop which was the coffee drive thru for wake-up drinks for my wife Liz and I encountered yet another young man at the drive thru window who was at least honest with me. I asked him how he was doing, and he said he was looking for a cot to lay down on to take a nap. I just looked at him and before I could say anything, he quickly said what I was thinking. He was working in a coffee shop, stop and get a cup to wake up.

One way or another, we made small talk, and I was again on my way, this time back home and he had acted as if nothing was wrong with how I was presenting as a transgender woman.

At least, the short trip out this morning into a potentially difficult world built my confidence up that I could do it again when my wife Liz and I go on an extended vacation to New England in approximately a month. A vacation which will challenge me in many ways including restroom privileges.

The end result of this morning was, I need more public adventures into potentially difficult situations to enable me to build the all important confidence I used to have when I was spending more time in the world.

  

So Many Ways to Come Out

  Image from Nicola Dowie on UnSplash. Recently, I had a response from a young transgender man on how he should attempt to come out to the...